data_AUR
# 
_chem_comp.id                                    AUR 
_chem_comp.name                                  "AUROVERTIN B" 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C25 H32 O8" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        460.517 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     AUR 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1COW 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
AUR C1   C1   C 0 1 N N N 87.345 97.681  63.913 4.076  0.110  -4.460 C1   AUR 1  
AUR C2   C2   C 0 1 N N N 86.445 98.839  63.493 2.822  0.900  -4.078 C2   AUR 2  
AUR C3   C3   C 0 1 N N R 86.442 99.974  64.520 1.662  0.466  -4.961 C3   AUR 3  
AUR C4   C4   C 0 1 N N S 85.167 100.833 64.515 0.362  1.229  -4.616 C4   AUR 4  
AUR C5   C5   C 0 1 N N S 85.684 102.031 65.286 -0.673 0.277  -5.289 C5   AUR 5  
AUR C6   C6   C 0 1 N N S 86.913 102.273 64.397 -0.094 -1.080 -4.799 C6   AUR 6  
AUR C7   C7   C 0 1 N N S 86.597 102.719 62.963 -0.517 -1.145 -3.313 C7   AUR 7  
AUR C8   C8   C 0 1 N N S 85.539 101.967 62.271 0.197  -0.013 -2.575 C8   AUR 8  
AUR C20  C20  C 0 1 N N N 84.132 100.085 65.312 0.336  2.635  -5.232 C20  AUR 9  
AUR C21  C21  C 0 1 N N N 87.852 103.261 64.945 -0.571 -2.278 -5.619 C21  AUR 10 
AUR C24  C24  C 0 1 N N N 86.486 102.482 68.684 -1.694 0.281  -8.960 C24  AUR 11 
AUR C25  C25  C 0 1 N N N 85.629 102.589 67.530 -1.740 0.168  -7.458 C25  AUR 12 
AUR O3   O3   O 0 1 N N N 87.543 100.904 64.381 1.340  -0.920 -4.792 O3   AUR 13 
AUR O4   O4   O 0 1 N N N 84.612 101.323 63.221 0.125  1.234  -3.222 O4   AUR 14 
AUR O5   O5   O 0 1 N N N 85.966 101.656 66.561 -0.630 0.386  -6.735 O5   AUR 15 
AUR O7   O7   O 0 1 N N N 87.721 103.139 62.217 -0.134 -2.405 -2.757 O7   AUR 16 
AUR O25  O25  O 0 1 N N N 85.417 103.734 67.196 -2.775 -0.116 -6.904 O25  AUR 17 
AUR C9   C9   C 0 1 N N N 84.861 102.844 61.260 -0.429 0.118  -1.200 C9   AUR 18 
AUR C10  C10  C 0 1 N N N 84.905 102.838 59.993 0.319  -0.045 -0.107 C10  AUR 19 
AUR C11  C11  C 0 1 N N N 84.059 103.735 59.204 -0.284 0.081  1.217  C11  AUR 20 
AUR C12  C12  C 0 1 N N N 84.039 103.645 57.900 0.475  -0.084 2.328  C12  AUR 21 
AUR C13  C13  C 0 1 N N N 83.307 104.621 57.070 -0.106 0.038  3.606  C13  AUR 22 
AUR C14  C14  C 0 1 N N N 83.321 104.576 55.742 0.654  -0.128 4.718  C14  AUR 23 
AUR C15  C15  C 0 1 Y N N 82.591 105.424 54.855 0.069  -0.005 6.001  C15  AUR 24 
AUR C16  C16  C 0 1 Y N N 82.584 105.392 53.494 0.850  -0.176 7.127  C16  AUR 25 
AUR C17  C17  C 0 1 Y N N 81.782 106.335 52.817 0.266  -0.053 8.397  C17  AUR 26 
AUR C18  C18  C 0 1 Y N N 81.027 107.262 53.440 -1.087 0.237  8.487  C18  AUR 27 
AUR C19  C19  C 0 1 Y N N 81.082 107.233 54.882 -1.831 0.400  7.315  C19  AUR 28 
AUR C22  C22  C 0 1 N N N 83.444 104.371 52.740 2.317  -0.491 6.993  C22  AUR 29 
AUR C23  C23  C 0 1 N N N 80.977 107.130 50.705 0.133  -0.030 10.629 C23  AUR 30 
AUR O15  O15  O 0 1 Y N N 81.847 106.360 55.517 -1.242 0.282  6.111  O15  AUR 31 
AUR O17  O17  O 0 1 N N N 81.830 106.228 51.456 1.011  -0.217 9.517  O17  AUR 32 
AUR O19  O19  O 0 1 N N N 80.453 108.023 55.600 -3.022 0.657  7.384  O19  AUR 33 
AUR H11A 1H1  H 0 0 N N N 87.347 96.854  63.164 4.322  0.302  -5.504 H11A AUR 34 
AUR H12A 2H1  H 0 0 N N N 88.381 98.033  64.126 4.907  0.421  -3.827 H12A AUR 35 
AUR H13A 3H1  H 0 0 N N N 87.071 97.305  64.926 3.891  -0.954 -4.320 H13A AUR 36 
AUR H21  1H2  H 0 1 N N N 86.718 99.214  62.479 2.576  0.707  -3.034 H21  AUR 37 
AUR H22  2H2  H 0 1 N N N 85.409 98.486  63.279 3.006  1.965  -4.218 H22  AUR 38 
AUR H3   H3   H 0 1 N N N 86.525 99.404  65.474 1.915  0.647  -6.012 H3   AUR 39 
AUR H5   H5   H 0 1 N N N 85.030 102.922 65.432 -1.677 0.449  -4.904 H5   AUR 40 
AUR H7   H7   H 0 1 N N N 86.056 103.686 63.085 -1.596 -1.020 -3.231 H7   AUR 41 
AUR H8   H8   H 0 1 N N N 86.001 101.123 61.707 1.240  -0.307 -2.420 H8   AUR 42 
AUR H201 1H20 H 0 0 N N N 83.207 100.708 65.308 1.099  3.254  -4.759 H201 AUR 43 
AUR H202 2H20 H 0 0 N N N 83.962 99.045  64.944 0.537  2.567  -6.302 H202 AUR 44 
AUR H203 3H20 H 0 0 N N N 84.477 99.818  66.338 -0.644 3.083  -5.075 H203 AUR 45 
AUR H211 1H21 H 0 0 N N N 88.744 103.436 64.299 -0.164 -3.195 -5.194 H211 AUR 46 
AUR H212 2H21 H 0 0 N N N 87.329 104.221 65.164 -1.660 -2.321 -5.600 H212 AUR 47 
AUR H213 3H21 H 0 0 N N N 88.162 102.978 65.977 -0.230 -2.173 -6.649 H213 AUR 48 
AUR H241 1H24 H 0 0 N N N 86.215 103.232 69.463 -2.683 0.072  -9.370 H241 AUR 49 
AUR H242 2H24 H 0 0 N N N 86.487 101.446 69.097 -1.391 1.290  -9.240 H242 AUR 50 
AUR H243 3H24 H 0 0 N N N 87.562 102.556 68.402 -0.977 -0.436 -9.357 H243 AUR 51 
AUR HO7  HO7  H 0 1 N N N 87.525 103.415 61.329 -0.416 -2.401 -1.833 HO7  AUR 52 
AUR H9   H9   H 0 1 N N N 84.179 103.677 61.501 -1.481 0.345  -1.106 H9   AUR 53 
AUR H10  H10  H 0 1 N N N 85.629 102.102 59.603 1.371  -0.271 -0.202 H10  AUR 54 
AUR H11  H11  H 0 1 N N N 83.401 104.520 59.613 -1.336 0.308  1.312  H11  AUR 55 
AUR H12  H12  H 0 1 N N N 84.613 102.784 57.517 1.527  -0.311 2.233  H12  AUR 56 
AUR H13  H13  H 0 1 N N N 82.701 105.449 57.474 -1.158 0.264  3.701  H13  AUR 57 
AUR H14  H14  H 0 1 N N N 83.981 103.783 55.350 1.706  -0.355 4.623  H14  AUR 58 
AUR H18  H18  H 0 1 N N N 80.430 107.966 52.836 -1.561 0.337  9.452  H18  AUR 59 
AUR H221 1H22 H 0 0 N N N 83.438 104.344 51.625 2.760  -0.589 7.984  H221 AUR 60 
AUR H222 2H22 H 0 0 N N N 84.499 104.480 53.082 2.439  -1.427 6.446  H222 AUR 61 
AUR H223 3H22 H 0 0 N N N 83.189 103.352 53.116 2.814  0.313  6.451  H223 AUR 62 
AUR H231 1H23 H 0 0 N N N 81.016 107.042 49.594 0.690  -0.153 11.557 H231 AUR 63 
AUR H232 2H23 H 0 0 N N N 79.922 107.025 51.052 -0.293 0.972  10.591 H232 AUR 64 
AUR H233 3H23 H 0 0 N N N 81.187 108.182 51.006 -0.668 -0.767 10.586 H233 AUR 65 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
AUR C1  C2   SING N N 1  
AUR C1  H11A SING N N 2  
AUR C1  H12A SING N N 3  
AUR C1  H13A SING N N 4  
AUR C2  C3   SING N N 5  
AUR C2  H21  SING N N 6  
AUR C2  H22  SING N N 7  
AUR C3  C4   SING N N 8  
AUR C3  O3   SING N N 9  
AUR C3  H3   SING N N 10 
AUR C4  C5   SING N N 11 
AUR C4  C20  SING N N 12 
AUR C4  O4   SING N N 13 
AUR C5  C6   SING N N 14 
AUR C5  O5   SING N N 15 
AUR C5  H5   SING N N 16 
AUR C6  C7   SING N N 17 
AUR C6  C21  SING N N 18 
AUR C6  O3   SING N N 19 
AUR C7  C8   SING N N 20 
AUR C7  O7   SING N N 21 
AUR C7  H7   SING N N 22 
AUR C8  O4   SING N N 23 
AUR C8  C9   SING N N 24 
AUR C8  H8   SING N N 25 
AUR C20 H201 SING N N 26 
AUR C20 H202 SING N N 27 
AUR C20 H203 SING N N 28 
AUR C21 H211 SING N N 29 
AUR C21 H212 SING N N 30 
AUR C21 H213 SING N N 31 
AUR C24 C25  SING N N 32 
AUR C24 H241 SING N N 33 
AUR C24 H242 SING N N 34 
AUR C24 H243 SING N N 35 
AUR C25 O5   SING N N 36 
AUR C25 O25  DOUB N N 37 
AUR O7  HO7  SING N N 38 
AUR C9  C10  DOUB N E 39 
AUR C9  H9   SING N N 40 
AUR C10 C11  SING N N 41 
AUR C10 H10  SING N N 42 
AUR C11 C12  DOUB N E 43 
AUR C11 H11  SING N N 44 
AUR C12 C13  SING N N 45 
AUR C12 H12  SING N N 46 
AUR C13 C14  DOUB N E 47 
AUR C13 H13  SING N N 48 
AUR C14 C15  SING N N 49 
AUR C14 H14  SING N N 50 
AUR C15 C16  DOUB Y N 51 
AUR C15 O15  SING Y N 52 
AUR C16 C17  SING Y N 53 
AUR C16 C22  SING N N 54 
AUR C17 C18  DOUB Y N 55 
AUR C17 O17  SING N N 56 
AUR C18 C19  SING Y N 57 
AUR C18 H18  SING N N 58 
AUR C19 O15  SING Y N 59 
AUR C19 O19  DOUB N N 60 
AUR C22 H221 SING N N 61 
AUR C22 H222 SING N N 62 
AUR C22 H223 SING N N 63 
AUR C23 O17  SING N N 64 
AUR C23 H231 SING N N 65 
AUR C23 H232 SING N N 66 
AUR C23 H233 SING N N 67 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
AUR SMILES           ACDLabs              10.04 O=C1OC(=C(C(OC)=C1)C)\C=C\C=C\C=C\C3OC2(C(OC(=O)C)C(OC2CC)(C3O)C)C                                                                                                                                      
AUR InChI            InChI                1.02b InChI=1/C25H32O8/c1-7-20-24(4)23(30-16(3)26)25(5,33-20)22(28)18(32-24)13-11-9-8-10-12-17-15(2)19(29-6)14-21(27)31-17/h8-14,18,20,22-23,28H,7H2,1-6H3/b9-8+,12-10+,13-11+/t18-,20+,22-,23+,24-,25-/m0/s1 
AUR InChIKey         InChI                1.02b QXCOFYWOWZJFEA-YJMRODJJBA                                                                                                                                                                               
AUR SMILES_CANONICAL CACTVS               3.341 CC[C@H]1O[C@@]2(C)[C@@H](O)[C@@H](O[C@]1(C)[C@H]2OC(C)=O)\C=C\C=C\C=C\C3=C(C)C(=CC(=O)O3)OC                                                                                                             
AUR SMILES           CACTVS               3.341 CC[CH]1O[C]2(C)[CH](O)[CH](O[C]1(C)[CH]2OC(C)=O)C=CC=CC=CC3=C(C)C(=CC(=O)O3)OC                                                                                                                          
AUR SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 CC[C@@H]1[C@]2([C@H]([C@@](O1)([C@H]([C@@H](O2)\C=C\C=C\C=C\C3=C(C(=CC(=O)O3)OC)C)O)C)OC(=O)C)C                                                                                                         
AUR SMILES           "OpenEye OEToolkits" 1.5.0 CCC1C2(C(C(O1)(C(C(O2)C=CC=CC=CC3=C(C(=CC(=O)O3)OC)C)O)C)OC(=O)C)C                                                                                                                                      
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
AUR "SYSTEMATIC NAME" ACDLabs              10.04 (1S)-4-O-acetyl-1,5:3,6-dianhydro-7,8-dideoxy-1-[(1E,3E,5E)-6-(4-methoxy-5-methyl-2-oxo-2H-pyran-6-yl)hexa-1,3,5-trien-1-yl]-3,5-dimethyl-D-glycero-L-talo-octitol          
AUR "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[(1S,3S,4S,5S,7R,8S)-7-ethyl-4-hydroxy-3-[(1E,3E,5E)-6-(4-methoxy-3-methyl-6-oxo-pyran-2-yl)hexa-1,3,5-trienyl]-1,5-dimethyl-2,6-dioxabicyclo[3.2.1]octan-8-yl] ethanoate" 
# 
